(2R)-pyrrolidine-2-carboxylic acid

• ChemBase ID: 2566
• Molecular Formular: C5H9NO2
• Molecular Mass: 115.13046
• Monoisotopic Mass: 115.06332853
• SMILES: OC(=O)[C@H]1CCCN1
• Canonical SMILES: OC(=O)[C@H]1CCCN1
• InChI: InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1
• InChIKey: ONIBWKKTOPOVIA-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: D-proline
• Synonyms: (R)-Pyrrolidine-2-carboxylic acid; D-Proline; H-D-Pro-OH; D-Proline; D-Proline; (2R)-2-Carboxypyrrolidine; (2R)-Pyrrolidine-2-carboxylic acid; (+)-(R)-Proline; (R)-(+)-Proline; (R)-2-Carboxypyrrolidine; (R)-Proline; D-(+)-Proline; D-Pyrrolidine-2-carboxylic acid; (+)-Z-D-proline; (R)-吡咯烷-2-羧酸; D-脯氨酸

Database IDs

• CAS Number: 6404-31-5; 344-25-2
• EC Number: 206-452-7
• MDL Number: MFCD00064317
• Beilstein Number: 80811
• PubChem SID: 46504839; 24887884; 160966016; 24888479
• PubChem CID: 8988; 145742

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.9406707
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.5687168
• LogD (pH = 7.4): -2.5686643
• Log P: -2.5686383
• Molar Refractivity: 28.0643 cm^3
• Polarizability: 11.294152 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.71
• LOG S: 0.5
• Solubility (Water): 3.65e+02 g/l

PROPERTIES

Physical Property

• Melting Point: 213-215°C dec.; 220-223 °C; 223 °C (dec.)(lit.); 223(dec.)°C
• Density: 1.36
• Optical Rotation: [α]20/D +85±2°, c = 5% in H2O; [α]22/D +85.0°, c = 4 in H2O; +84 (c=1 in water)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic; IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; ≥99%; ≥99.0% (NT); 95+%; 97%; 98%; 99%
• Grade: puriss.; ReagentPlus®
• Optical Purity: ee: 98% (GLC)
• Empirical Formula (Hill Notation): C5H9NO2

DETAILS

MP Biomedicals - 02195456

Crystalline
Purity: 99+%

DrugBank - DB02853

• Drug Groups: experimental
• Description: A non-essential amino acid that is synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons. [PubChem]

Sigma Aldrich - 858919

Packaging
5 g in glass bottle
500 mg in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 858919.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 81705

Other Notes
Asymmetric self-condensation of β-ionylideneacetaldehyde, retinal and related compounds1

Toronto Research Chemicals - P755990

Used in the synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine and formal synthesis of (-)-Lasubine II and (+)-Cermizine C.

REFERENCES

• Gawley, R., et al.: Org. Biomol. Chem., 4, 4285 (2006)